Hydrochloric Acid → (S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acid

HRID 714129

反応式

HRID 714129 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH2:12])[C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].Cl[C:19]([O:21][CH3:22])=[O:20].Cl>C1COCC1>[CH3:22][O:21][C:19]([NH:12][C@H:8]([C:9]([OH:11])=[O:10])[CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[O:20]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 6586Methyl chloroformateHCID 516892Sodium Bicarbonate

生成物 1

HCID 10017620(S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acid収率 198.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A suspension of L-diphenylalanine (13.87 g, 57.5 mmol) in THF (100 ml), and saturated NaHCO3 (3 mL) stirred at 0° C. was treated with neat methyl chloroformate (11.81 g, 125 mmol) (slow addition), stirred at the same temperature for 10 min and then at room temperature for 14 h, made acidic by addition of 1M HCl and extracted with DCM, dried over MgSO4 filtered and concentrated to give title compound (17.1 g, 99% yield) as white solid. Used without further purification. MS: m/z=322.1 (MNa+).

後処理

  1. stirringstirred at the same temperature for 10 min
  2. extractionextracted with DCM
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-1920437b70054c55954a76cd97adb72e
出典データセット
uspto-grants-2015_11
特許番号
US09187415B2

関連ノート

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